1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study

Aleksey Yu Vorob′ev, Gennady I. Borodkin, Rodion V. Andreev, Vyacheslav G. Shubin

Research output: Contribution to journalArticlepeer-review

Abstract

Series of 2-pyridyl[1,2,4]triazolo[1,5-a]azines have been synthesized by cycloaddition of cyanopyridines with N-aminoazinium mesitylenesulfonates under basic conditions (KOH/H2O). An improved protocol for pyridyl-substituted [1,2,4]triazolo[1,5-a]pyridines synthesis based on addition of H2O2 as internal oxidant has been suggested. In the case of quinolinium and isoquinolinium salts, only dimerization of the corresponding N-imines has been observed, while pyrazinium-N-imine has not shown any reactivity toward cycloaddition. DFT studies have shown that the cycloaddition proceeds through concerted mechanism.

Original languageEnglish
Pages (from-to)284-291
Number of pages8
JournalChemistry of Heterocyclic Compounds
Volume57
Issue number3
DOIs
Publication statusPublished - Mar 2021

Keywords

  • 1,3-dipolar cycloaddition
  • DFT
  • N-imines
  • [1,2,4]triazolo[1,5-a]azines

OECD FOS+WOS

  • 1.04 CHEMICAL SCIENCES
  • 1.04.EE CHEMISTRY, ORGANIC

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